Holiday houses in Southern Maryland
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Top-rated holiday rentals in Southern Maryland
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Southern Maryland holiday rentals
Other great holiday rentals in Southern Maryland
Guest favourite
Cabin in Lusby
4.91 out of 5 average rating, 215 reviewsPeaceful Waterfront Retreat on The Bay
Guest favourite
Farm stay in Madison
4.98 out of 5 average rating, 169 reviewsMadison Nature Getaway
Guest favourite
Cottage in Leonardtown
4.93 out of 5 average rating, 128 reviewsBreton Breeze
Guest favourite
Rental unit in Lusby
4.96 out of 5 average rating, 168 reviewsTerrace Suite - Private Flat in Historic Manor.
Guest favourite
Home in Lusby
5 out of 5 average rating, 114 reviewsHistoric Rousby Hall, Waterfront, Patuxent River
Guest favourite
Guesthouse in Bushwood
4.93 out of 5 average rating, 148 reviewsLittle House by the water
Guest favourite
Cottage in Colonial Beach
4.93 out of 5 average rating, 198 reviewsCozy cottage 3 blocks from beach
Guest favourite
Home in Lusby
4.98 out of 5 average rating, 266 reviewsCove Point Beach Cabin
Destinations to explore
- Baltimore Accommodation & holiday rentals
- Ocean City Accommodation & holiday rentals
- Richmond Accommodation & holiday rentals
- Rehoboth Beach Accommodation & holiday rentals
- Arlington Accommodation & holiday rentals
- Charlottesville Holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
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- Jersey City Holiday rentals
- The Hamptons Holiday rentals
- Smoking-friendly rentals Southern Maryland
- Rentals with lake access Southern Maryland
- Kid-friendly rentals Southern Maryland
- Rentals with an EV charger Southern Maryland
- Rentals with a fire pit Southern Maryland
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- Apartment rentals Southern Maryland
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- Rentals with a hot tub Southern Maryland
- Guesthouse rentals Southern Maryland
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- Rentals with beach access Southern Maryland
- Waterfront rentals Southern Maryland
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